2-Amino-2-methyl-1-propanol → HCID 43500201, compound

HRID 1716378Notes

Reaction equation

HRID 1716378 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[NH2:12][C:13]([CH3:17])([CH3:16])[CH2:14][OH:15]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13]([CH3:17])([CH3:16])[CH2:14][OH:15])=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 43500201HCID 43500201, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As shown in Scheme ??, mix 5-bromo-2-fluoronitrobenzene (11.2 g, 50.5 mmol) and 2-amino-2-methyl-1-propanol (10.5 mL, 110 mmol) in THF (120 mL). Heat at reflux for 48 h and then cool to room temperature. Remove most of the THF under reduced pressure and then partition the residue between water and EtOAc. Wash the organic layer a second time with water and the dry (MgSO4) and concentrate to give an orange solid. Triturate the solid with hexane (200 mL) and dry to yield 12.95 g (89%) title compound. MS (es) 288 (M−1). HPLC (ISO80-10M) t=2.67 (100%).

Workup

  1. temperatureHeat
  2. temperatureat reflux for 48 h
  3. customRemove most of the THF under reduced pressure
  4. custompartition the residue between water and EtOAc
  5. washWash the organic layer a second time with water
  6. dry with materialthe dry (MgSO4)
  7. concentrationconcentrate
  8. customto give an orange solid
  9. customTriturate the solid with hexane (200 mL)
  10. customdry

Sources & evidence

ORD record
ord-62094d05c54b40f7b6f807fde479eed4
Source dataset
uspto-grants-2010_09
Patent number
US07803814B2

Reaction notes

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